US3677726A - Monosubstituted ureas as fuel additives - Google Patents

Monosubstituted ureas as fuel additives Download PDF

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Publication number
US3677726A
US3677726A US60639A US3677726DA US3677726A US 3677726 A US3677726 A US 3677726A US 60639 A US60639 A US 60639A US 3677726D A US3677726D A US 3677726DA US 3677726 A US3677726 A US 3677726A
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fuel
ureas
urea
varnish
monosubstituted
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Aubert Y Coran
Billy D Vineyard
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Monsanto Co
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Monsanto Co
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2227—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond urea; derivatives thereof; urethane
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    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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    • C10M2203/102—Aliphatic fractions
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
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Definitions

  • This invention relates to additives for liquid hydrocarbon fuels. More specifically, it relates to hydrocarbon fuel compositions having improved varnish-removing and lacquer-removing characteristics.
  • Liquid hydrocarbon fuels have a tendency to form polymeric materials known as gum. Gum, which is often formed during storage of the fuel, leads to resin-like deposits in various parts of fuel systems. For example, in the case of internal combustion engines, resin-like deposits tend to form in the fuel supply lines, fuel filter, carburetor, fuel control, injectors, intake manifold and valve stems. Such deposits are objectionable not only because of their effect on mechanical performance, but also because they decrease the breathing efficiency in engines of the spark ignition type.
  • Hydrocarbon fuels for internal combustion engines may be broadly classified in four categories according to the use for which they are intended; fuels for automotive spark ignition engines, fuels for aircraft spark ignition engines, fuels for gas turbine engines and fuels for compression ignition engines. Although each such fuel is composed essentially of hydrocarbons, the stability characteristics during the manufacturing process and subsequent storage and use, particularly in the presence of oxygen, differ considerably for each type. For example, typical automotive fuels contain straight and branched chain aliphatics, olefins, naphthenes and some aromatics, while typical aircraft fuels contain a smaller proportion of olefins. In recent years, fuels for compression ignition engines have contained an increased proportion of cracked stocks, resulting in a higher olefin content and a consequent increase in the susceptibility to the formation of gum.
  • liquid hydrocarbon fuel as used herein, is intended to embrace distillate fuel oils as well as fuels for internal combustion engines. It is well known that fuel oils are prone to form gum during periods of prolonged storage. This results in formation of resin-like deposits on equipment parts such as noz zles, screens, fuel lines, filters and the like, thereby causing eventual blockage or sticking and malfunctioning of the equipment.
  • the prior art discloses various fuel additives designed to retard the formation of gum.
  • the present invention discloses a particular class of fuel additives which is effective in removing lacquer and varnish deposits attributable to gum after they have formed, thus behaving as a varnish stripper.
  • the monosubstituted urea compounds which are employed as fuel additives in the present invention are represented by the following structure:
  • R is hydrogen, alkyl or alkenyl and R is alkyl or alkenyl, and the sum of the carbon atoms in R and R is from about 5 to about 25 and H O R(i7NHfl-NH2 1'1 where R is alkyl or alkenyl having from 5 to 25 carbon atoms.
  • Preferred compounds are those monosubstituted ureas where the substituent group is primary alkyl or primary alkenyl having at least about 9 carbon atoms. Outstanding results have been achieved, with octadecylurea, dodecylurea and 9-octadecenyl urea.
  • a stainless steel spatula was coated in the following manner with resinous deposits from a Sequence VB test engine which had operated on a mineral lubricating oil. This type test is one of the group known as the Engine Test Sequences for Evaluating Oils for API Service MS (1963). The spatula was dipped into dimethylformamide solvent containing approximately 20% by weight of the resinous deposits, and the coating was then allowed to dry. The coated spatula was then immersed in the hot oil-urea solution for 30 minutes, removed, allowed to cool and wiped with a tissue. The portion of resin removed after wiping was visually estimated and defined as the activity percentage. Results obtained with various substituted urea compounds are set forth in Table I below wherein the substituent groups correspond to the following structure:
  • Another process comprises reacting an alkyl amine with urea in approximately equivalent molecular proportions and then heating the mixture to a temperature between 100 C. and the decomposition temperature of the desired alkyl urea.
  • Yet another process comprises the reaction of carbon monoxide, sulfur and an amine.
  • G 9 1-(Z-tert-butyl-5,6-dimethylcyclohexy1-3,3-dimethyluread(i11 ⁇ -f-ufi5,)6- H -CH; -C H3 10 e o s 1-(2-tert-butyl fi-etbylcyclohexyl-3,3-dimethylurea Egg-guid- H -CH; -CH; 0
  • EXAMPLE 1 9-octadecenylurea was added to gasoline at concentrations from p.p.m. to 100 p.p.m., being solubilized by either isopropanol or alkylbenzene (C sulfonic acid.
  • a single-cylinder CLR Oil Test Engine having resin-like deposits on the carburetor threat was operated on the urea-containing gasoline for approximately 24 hours. Visual inspection of the carburetor throat following the test run revealed that significant cleaning had occurred.
  • Monosubstituted ureas useful in the fuel compositions of the present invention may be prepared according to numerous known processes. Processes for the manufacture of monoalkylsubstituted ureas have involved the reaction of alkyl isocyanates with ammonia, the reaction of ammonium salts with alkali metal cyanates and the reaction of nitrourea with amines.
  • Still another process present in the monosu bstituted ureas of the present invention are alkyl radicals, e.g., amyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and other branched alkyl radicals having the formula where n is an integer up to 25; alkenyl radicals, e.g., pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl and other alkenyl radicals having the formula C lwhere n is an integer up to 25.
  • alkyl radicals e.g., amyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl
  • the additives of the present invention find utility in distillate fuel oils as well as in gasoline.
  • the fuel oils that are included within the present invention are hydrocarbon fractions having an initial boiling point of at least about F. and an end boiling point no higher than about 750 F., and boiling substantially continuously throughout their distillation range.
  • the distillate fuel oils can be straight-run distillate fuel oils, catalytically or thermally cracked (including hydrocracked) distillate fuel oils, or mixtures of straightrun distillate fuel oils, naphthas and the like, with cracked distillate stocks.
  • Particularly contemplated among the fuel oils are Nos. 1, 2 and 3 fuel oils used in heating and as diesel fuel oils, and the jet combustion fuels.
  • the domestic fuel oils generally conform to the specifications set forth in ASTM Specifications D396-48T.
  • Specifications for diesel fuels are defined in ASTM Specifications D975-48T.
  • Straight run gasoline 2 Benzene 12 Toluene 8 Butanes 12 (ASTM distillation range of 80 F. to 290 F. and a midboiling point of 200 F.)
  • the monosubstituted ureas of the present invention may be used in motor gasoline along with other additives designed to impart other improved properties thereto.
  • anti-knock agents pre-ignition inhibitors, anti-rust agents, metal-deactivators, dyes, antioxidants, detergents, antistall agents, etc.
  • the gasoline may contain a small amount, from about 0.01 percent to about 1 percent, by weight, of a solvent oil or upperlube.
  • Suitable oils include Coastal and Mid-Continent distillate oils having viscosities within the range of from about 50 to about 500 S.U.S. at 100 F.
  • Synthetic oils such as diester oils, polyalkylene glycols, silicones, phosphate esters, polypropylenes, polybutylenes and the like, may also be used.
  • the fuel oil composition can contain other additives for the purpose of achieving other results.
  • foam inhibitors and ignition and burning quality improvers are present.
  • examples of such additives are silicons, dinitropropane, amyl nitrate, metal sulfonates and the like.
  • Those monosubstituted ureas of the present invention which are not soluble in fuel at room temperature can be solubilized by small amounts of strong acid (0.5 mole of HCl or 1 mole of benzene sulfonic acid) or larger amounts of weak acids (approximately 2 to 3 moles of acetic acid).
  • strong acid 0.5 mole of HCl or 1 mole of benzene sulfonic acid
  • weak acids approximately 2 to 3 moles of acetic acid
  • the urea additive may be used on an intermittent basis in some applications and on a continuous basis in others.
  • the intermittent application would usually employ a greater concentration of urea additive, e.g., 25 p.p.m. to 300 p.p.m., particularly p.p.m. or more, in a limited batch of fuel. After the batch of urea-containing fuel is consumed and the fuel induction and air induction system is cleaned, operation on standard fuel would resume.
  • a fuel composition comprising a major amount of a liquid hydrocarbon fuel and a minor amount, sufiicient to impart varnish-removing activity, of a compound having the formula where R is alkyl or alkenyl having from 5 to 25 carbon atoms.
  • composition of claim 1 wherein the compound is octadecylurea.
  • composition of claim 1 wherein the compound is dodecylurea.
  • composition of claim 1 wherein the compound is 9-octadecenylurea.
  • composition of claim 1 wherein the fuel is a hydrocarbon mixture boiling in the gasoline boiling range.
  • composition of claim 1 wherein the fuel is a distillate fuel oil.
  • composition of claim 1 wherein the compound is present in a concentration from about 25 p.p.m. to about 300 p.p.m. based upon the fuel.

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5286266A (en) * 1992-07-09 1994-02-15 Texaco Inc. Motor fuel detergent additives - asymmetrical ureas of hydrocarbyloxypolyether amines and tertiary aminoalkyl primary amines
US5997593A (en) * 1998-12-22 1999-12-07 Ethyl Corporation Fuels with enhanced lubricity
US20040010963A1 (en) * 2002-07-16 2004-01-22 Betzdearborn, Inc. Lubricity additives for low sulfur hydrocarbon fuels
WO2004022530A1 (en) * 2002-09-05 2004-03-18 Dbl Australia Pty Ltd Urea-, glycerate- and, hydroxyamide-headed hydrocarbon chain lyotropic phases forming surfactants
US20060172900A1 (en) * 2003-10-16 2006-08-03 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
RU2314334C1 (ru) * 2006-07-25 2008-01-10 Ара Аршавирович Абрамян Присадка к моторному топливу
RU2320708C1 (ru) * 2006-09-25 2008-03-27 Закрытое акционерное общество "Институт прикладной нанотехнологии" Присадка к моторному топливу

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US3993842A (en) 1973-04-24 1976-11-23 E. I. Du Pont De Nemours And Company Electrically conductive elastomeric ink
US4919833A (en) * 1987-05-21 1990-04-24 Ciba-Geigy Corporation Functional fluids
EP1667656A4 (en) * 2003-09-01 2011-12-28 Mayne Pharma Int Pty Ltd COMPOSITIONS AND METHODS OF DISTRIBUTING BIOLOGICALLY ACTIVE AGENTS
JP4486339B2 (ja) * 2003-10-16 2010-06-23 新日本石油株式会社 潤滑油組成物
DE102004006304A1 (de) * 2004-02-09 2005-08-25 Basf Ag Hochfunktionelle, hochverzweigte Polyharnstoffe
WO2016191208A1 (en) 2015-05-22 2016-12-01 Cummins Inc. Unique oil as a service event
CN113337318B (zh) * 2021-06-08 2023-05-30 盛世昆仲(北京)科技发展有限公司 一种节能环保燃料油的制备方法

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5286266A (en) * 1992-07-09 1994-02-15 Texaco Inc. Motor fuel detergent additives - asymmetrical ureas of hydrocarbyloxypolyether amines and tertiary aminoalkyl primary amines
US5997593A (en) * 1998-12-22 1999-12-07 Ethyl Corporation Fuels with enhanced lubricity
US20050126073A1 (en) * 2002-07-16 2005-06-16 Betzdearborn, Inc. Lubricity additives for low sulfur hydrocarbon fuels
US20040010963A1 (en) * 2002-07-16 2004-01-22 Betzdearborn, Inc. Lubricity additives for low sulfur hydrocarbon fuels
US6872230B2 (en) 2002-07-16 2005-03-29 Betzdearborn, Inc. Lubricity additives for low sulfur hydrocarbon fuels
US20050249665A1 (en) * 2002-09-05 2005-11-10 Dbl Australia Pty Ltd. Urea-, glycerate- and, hydroxyamide-headed hydrocarbon chain lyotropic phases forming surfactants
WO2004022530A1 (en) * 2002-09-05 2004-03-18 Dbl Australia Pty Ltd Urea-, glycerate- and, hydroxyamide-headed hydrocarbon chain lyotropic phases forming surfactants
KR100948890B1 (ko) * 2002-09-05 2010-03-24 메인 파마 인터내셔널 프로프라이어터리 리미티드 계면활성제를 형성하는 우레아-, 글리세레이트- 및, 히드록시아미드-머리의 탄화수소 사슬 농도전이형 상
US20060172900A1 (en) * 2003-10-16 2006-08-03 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
EP2343355A1 (en) * 2003-10-16 2011-07-13 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
US8481467B2 (en) 2003-10-16 2013-07-09 Nippon Oil Corporation Lubricating oil additive and lubricating oil composition
RU2314334C1 (ru) * 2006-07-25 2008-01-10 Ара Аршавирович Абрамян Присадка к моторному топливу
RU2320708C1 (ru) * 2006-09-25 2008-03-27 Закрытое акционерное общество "Институт прикладной нанотехнологии" Присадка к моторному топливу

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DE2138569A1 (de) 1972-02-10
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BE770829A (fr) 1971-12-16
US3706667A (en) 1972-12-19
DE2138569B2 (de) 1974-06-06
GB1353561A (en) 1974-05-22
DE2138569C3 (de) 1975-01-30
CA953499A (en) 1974-08-27
JPS5035081B1 (enExample) 1975-11-13

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